Oxidative and nitrative modifications of enkephalins by reactive nitrogen species

References

• Hughes J, Smith TW, Kosterlitz HW, Fothergill LA, Morris HR. Identification of two related pentapeptides from the brain with potent opiate agonist activity. Nature 1975; 258: 577–579
   PubMed Web of Science ®Google Scholar
• Frederickson RCA. Enkephalin pentapeptides. A review of current evidence for a physiological role in vertebrate neurotransmission. Life Sci 1977; 21: 23–42
   PubMed Web of Science ®Google Scholar
• Hambrook JM, Morgan BA, Rance MJ, Smith CF. Mode of deactivation of the enkephalins by rat and human plasma and rat brain homogenates. Nature 1976; 262: 782–783
   PubMed Web of Science ®Google Scholar
• Erdos EG, Skidgel RA. Neutral endopeptidase 24.11 (enkephalinase) and related regulators of peptide hormones. FASEB J 1989; 3: 145–151
   PubMed Web of Science ®Google Scholar
• Terenius L, Wahlstrom A, Lindeberg G, Karlsson S, Ragnarsson U. Opiate receptor affinity of peptides related to Leu-enkephalin. Biochem Biophys Res Commun 1976; 71: 175–179
   PubMed Web of Science ®Google Scholar
• Rosei MA, Antonilli L, Coccia R, Foppoli C. Enkephalins and exorphins oxidation by tyrosinase. Biochem Int 1989; 19: 1183–1193
   PubMedGoogle Scholar
• Rosei MA, Blarzino C, Foppoli C, Coccia R, De Marco C. The peroxidase-catalyzed oxidation of enkephalins. Biochem Biophys Res Commun 1991; 179: 147–152
   PubMed Web of Science ®Google Scholar
• Larsimont V, Prokai L, Hochhaus G. Leucine enkephalin-tyrosinase reaction products—identification and biological activity. Biochim Biophys Acta 1994; 1222: 95–100
   PubMedGoogle Scholar
• Rosei MA, Mosca L, De Marco C. Melanins production from enkephalin by tyrosinase. Biochem Biophys Res Commun 1992; 184: 1190–1196
   PubMed Web of Science ®Google Scholar
• Rosei MA. Melanins from opioid peptides. Pigment Cell Res 1996; 9: 1–8
   Google Scholar
• Fontana M, Mosca L, Rosei MA. Interaction of enkephalins with oxyradicals. Biochem Pharmacol 2001; 61: 1253–1257
   PubMed Web of Science ®Google Scholar
• Rosei MA, Coccia R, Foppoli C, Blarzino C, Cini C, Schininà E. Cysteinyldopaenkephalins: Synthesis, characterization and binding to bovine brain opioid receptors. Biochim Biophys Acta 2000; 1478: 19–29
   PubMedGoogle Scholar
• Coccia R, Foppoli C, Blarzino C, De Marco C, Rosei MA. Interactions of enkephalin derivatives with reactive oxygen species. Biochim Biophys Acta 2001; 1525: 43–49
   PubMedGoogle Scholar
• Blarzino C, Mosca L, Foppoli C, Coccia R, De Marco C, Rosei MA. Lipoxygenase/H2O2-catalyzed oxidation of dihydroxyindoles: Synthesis of melanin pigments and study of their antioxidant properties. Free Radic Biol Med 1999; 26: 446–451
   PubMed Web of Science ®Google Scholar
• Rosei MA. Opiomelanins synthesis and properties. Histol Histopathol 2001; 16: 931–935
   PubMedGoogle Scholar
• Koppenol WH, Moreno JJ, Pryor WA, Ischiropoulos H, Beckman JS. Peroxynitrite, a cloaked oxidant formed by nitric oxide and superoxide. Chem Res Toxicol 1992; 5: 834–842
   PubMed Web of Science ®Google Scholar
• Huie RE, Padmaja S. The reaction of NO with superoxide. Free Radic Res Commun 1993; 18: 195–199
   PubMed Web of Science ®Google Scholar
• Pryor WA, Squadrito GL. The chemistry of peroxynitrite: A product from the reaction of nitric oxide with superoxide. Am J Physiol 1995; 268: L699–L722
   PubMed Web of Science ®Google Scholar
• Radi R, Peluffo G, Alvarez MN, Naviliat M, Cayota A. Unraveling peroxynitrite formation in biological system. Free Radic Biol Med 2001; 30: 463–488
   PubMed Web of Science ®Google Scholar
• Lymar SV, Hurst JK. Rapid reaction between peroxynitrite ion and carbon dioxide: Implications for biological activity. J Am Chem Soc 1995; 121: 10695–10701
   Google Scholar
• Denicola A, Freeman BA, Trujillo M, Radi R. Peroxynitrite reaction with carbon dioxide/bicarbonate: Kinetics and influence on peroxynitrite-mediated oxidations. Arch Biochem Biophys 1996; 333: 49–58
   PubMed Web of Science ®Google Scholar
• Meli R, Nauser T, Latal P, Koppenol WH. Reaction of peroxynitrite with carbon dioxide: Intermediates and determination of the yield of and . J Biol Inorg Chem 2002; 7: 31–36
   PubMed Web of Science ®Google Scholar
• Augusto O, Bonini MG, Amanso AM, Linares E, Santos CCX, De Menezes SL. Nitrogen dioxide and carbonate radical anion: Two emerging radicals in biology. Free Radic Biol Med 2002; 32: 841–859
   PubMed Web of Science ®Google Scholar
• Pfeiffer S, Schimdt K, Mayer B. Dityrosine formation outcompetes tyrosine nitration at low steady-state concentration of peroxynitrite. Implications for tyrosine modification by nitric oxide/superoxide in vivo. J Biol Chem 2000; 275: 6346–6352
   PubMedGoogle Scholar
• Thomas DD, Graham Espey M, Vitek MP, Miranda KM, Wink DA. Protein nitration is mediated by heme and free metals through Fenton-type chemistry: An alternative to the NO/ reaction. Proc Natl Acad Sci USA 2002; 99: 12691–12696
   PubMed Web of Science ®Google Scholar
• Radi R. Nitric oxide, oxidants, and protein nitration. Proc Natl Acad Sci USA 2004; 101: 4003–4008
   PubMed Web of Science ®Google Scholar
• Eiserich JP, Hristova M, Cross CE, Daniel Jones A, Freeman BA, Halliwell B, Van Der Vliet A. Formation of nitric oxide-derived oxidants by myeloperoxidase in neutrophils. Nature 1998; 391: 393–397
   PubMed Web of Science ®Google Scholar
• Brennan M-L, Wu W, Fu X, Shen Z, Song W, Frost H, Vadseth C, Narine L, Lenkiewicz E, Borchers MT, Lusis AJ, Lee JJ, Lee NA, Abu-Soud HM, Ischiropoulos H, Hazen SL. A tale of two controversies. Defining both the role of peroxidases in nitrotyrosine formation in vivo using eosinophil peroxidase and myeloperoxidase-deficient mice, and the nature of peroxidase-generated reactive nitrogen species. J Biol Chem 2002; 277: 17415–17427
   PubMed Web of Science ®Google Scholar
• Herold S. Nitrotyrosine, dityrosine, and nitrotryptophan formation from metmyoglobin, hydrogen peroxide, and nitrite. Free Radic Biol Med 2004; 36: 565–579
   PubMed Web of Science ®Google Scholar
• Pecci L, Montefoschi G, Antonucci A, Costa M, Fontana M, Cavallini D. Formation of nitrotyrosine by methylene blue photosensitized oxidation of tyrosine in the presence of nitrite. Biochem Biophys Res Commun 2001; 289: 305–309
   PubMedGoogle Scholar
• Greenacre SA, Ischiropoulos H. Tyrosine nitration: Localisation, quantification, consequences for protein function and signal transduction. Free Radic Res 2001; 34: 541–581
   PubMed Web of Science ®Google Scholar
• Eiserich JP, Patel RP, O'Donnell VB. Pathophysiology of nitric oxide and related species: Free radical reactions and modification of biomolecules. Mol Aspects Med 1998; 19: 221–357
   PubMedGoogle Scholar
• Ischiropoulos H. Biological tyrosine nitration: A pathophysiological function of nitric oxide and reactive oxygen species. Arch Biochem Biophys 1998; 356: 1–11
   PubMed Web of Science ®Google Scholar
• Beckman JS, Beckman TW, Chen J, Marshall PA, Freeman BA. Apparent hydroxyl radical production by peroxynitrite: Implications for endothelial injury from nitric oxide and superoxide. Proc Natl Acad Sci USA 1990; 87: 1620–1624
   PubMed Web of Science ®Google Scholar
• Beckman JS, Ye YZ, Anderson P, Chen J, Accavetti MA, Tarpey MM, White CR. Extensive nitration of protein tyrosine in human atherosclerosis detected by immunohistochemistry. Biol Chem 1994; 375: 81–88
   PubMed Web of Science ®Google Scholar
• Kaur H, Halliwell B. Evidence for nitric oxide-mediated oxidative damage in chronic inflammation. FEBS Lett 1994; 350: 9–12
   PubMed Web of Science ®Google Scholar
• Malencik DA, Sprouse JF, Swanson CA, Anderson SR. Dityrosine: Preparation, isolation, and analysis. Anal Biochem 1996; 242: 202–213
   PubMed Web of Science ®Google Scholar
• Beckman JS, Chen J, Ischiropoulos H, Crow JP. Oxidative chemistry of peroxynitrite. Meth Enzymol 1994; 233: 229–240
   PubMed Web of Science ®Google Scholar
• Feelisch M, Ostrowski J, Noack E. On the mechanism of NO release from sydnonimines. J Cardiovasc Pharmacol 1989; 14: S13–S22
   PubMedGoogle Scholar
• Kooy N, Royall JA, Ischiropoulos H, Beckman JS. Peroxynitrite-mediated oxidation of dihydrorhodamine 123. Free Radic Biol Med 1994; 16: 149–156
   PubMed Web of Science ®Google Scholar
• Beckman JS, Ischiropoulos H, Zhu L, van der Woerd M, Smith C, Chen J, Harrison J, Martin JC, Tsai M. Kinetics of superoxide dismutase- and iron-catalyzed nitration of phenolics by peroxynitrite. Arch Biochem Biophys 1992; 298: 438–445
   PubMed Web of Science ®Google Scholar
• Sampson JB, Ye Y, Rosen H, Beckman JS. Myeloperoxidase and horseradish peroxidase catalyze tyrosine nitration in proteins from nitrite and hydrogen peroxide. Arch Biochem Biophys 1998; 356: 207–213
   PubMed Web of Science ®Google Scholar
• Hogg N, Darley-Usmar VM, Wilson MT, Moncada S. Production of hydroxyl radicals from the simultaneous generation of superoxide and nitric oxide. Biochem J 1992; 281: 419–424
   PubMed Web of Science ®Google Scholar
• van der Vliet A, Eiserich JP, O'Neill CA, Halliwell B, Cross CE. Tyrosine modification by reactive nitrogen species: A closer look. Arch Biochem Biophys 1995; 319: 341–349
   PubMed Web of Science ®Google Scholar
• Prütz WA, Mönig H, Butler J, Land EJ. Reactions of nitrogen dioxide in aqueous model systems: Oxidation of tyrosine units in peptides and proteins. Arch Biochem Biophys 1985; 243: 125–134
   PubMed Web of Science ®Google Scholar
• Hunter EPL, Desrosiers MF, Simic MG. The effect of oxygen, antioxidants, and superoxide radical on tyrosine phenoxyl radical dimerization. Free Radic Biol Med 1989; 6: 581–585
   PubMed Web of Science ®Google Scholar
• Judd AK, Lawson JA, Olsen CM, Toll LR, Polgar WE, Uyeno ET, Keys CJ, Loew GH. Novel mu-selective Met-enkephalinamide analogs with antagonist activity. Synthesis, receptor binding, analgesic properties and conformational studies. Int J Pept Protein Res 1987; 30: 299–317
   PubMedGoogle Scholar
• Foppoli C, Coccia R, Blarzino C, Cini C, Rosei MA. Tetrahydroisoquinoline derivatives of enkephalins: Synthesis and properties. Biochem Pharmacol 2002; 63: 1885–1892
   PubMedGoogle Scholar
• Moosmann B, Behl C. Secretory peptide hormones are biochemical antioxidants: Structure–activity relationships. Mol Pharmacol 2002; 61: 260–268
   PubMed Web of Science ®Google Scholar